JPS6067443A - Method for stabilizing aliphatic halogenated carboxylic acid - Google Patents
Method for stabilizing aliphatic halogenated carboxylic acidInfo
- Publication number
- JPS6067443A JPS6067443A JP17647083A JP17647083A JPS6067443A JP S6067443 A JPS6067443 A JP S6067443A JP 17647083 A JP17647083 A JP 17647083A JP 17647083 A JP17647083 A JP 17647083A JP S6067443 A JPS6067443 A JP S6067443A
- Authority
- JP
- Japan
- Prior art keywords
- alpha
- acid
- hydroquinone
- carboxylic acid
- halogenated carboxylic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000001931 aliphatic group Chemical group 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 6
- 230000000087 stabilizing effect Effects 0.000 title claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title abstract description 4
- 239000002253 acid Substances 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract description 12
- 239000000203 mixture Substances 0.000 abstract description 6
- MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 abstract description 3
- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 abstract description 3
- IPLKGJHGWCVSOG-UHFFFAOYSA-N 4-chlorobutanoic acid Chemical compound OC(=O)CCCCl IPLKGJHGWCVSOG-UHFFFAOYSA-N 0.000 abstract description 3
- YAQLSKVCTLCIIE-UHFFFAOYSA-N 2-bromobutyric acid Chemical compound CCC(Br)C(O)=O YAQLSKVCTLCIIE-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 230000001976 improved effect Effects 0.000 abstract description 2
- 230000007774 longterm Effects 0.000 abstract description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- VMSLCPKYRPDHLN-UHFFFAOYSA-N (R)-Humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-UHFFFAOYSA-N 0.000 abstract 1
- 238000013019 agitation Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 239000011369 resultant mixture Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- -1 aliphatic halogen carboxylic acid Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QVHNPERSEFABEH-UHFFFAOYSA-N 2,2-dibromopropanoic acid Chemical compound CC(Br)(Br)C(O)=O QVHNPERSEFABEH-UHFFFAOYSA-N 0.000 description 1
- RVBUZBPJAGZHSQ-UHFFFAOYSA-N 2-chlorobutanoic acid Chemical compound CCC(Cl)C(O)=O RVBUZBPJAGZHSQ-UHFFFAOYSA-N 0.000 description 1
- RCDBVFJRWCGLIB-UHFFFAOYSA-N 3-hydroxy-6-methoxycyclohexa-2,4-dien-1-one Chemical group COC1C(C=C(O)C=C1)=O RCDBVFJRWCGLIB-UHFFFAOYSA-N 0.000 description 1
- NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、医農薬原料として有用な脂肪族ハロゲンカル
ボン酸を安定に保存する方法、具体的には経時白濁を防
止する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for stably preserving aliphatic halogencarboxylic acids useful as raw materials for medicines and agrochemicals, and specifically to a method for preventing clouding over time.
現状、脂肪族ハロゲンカルボン酸の工、業的製法として
は、脂肪族カルボン酸のハロゲン化によって得られる。At present, aliphatic halogencarboxylic acids are produced by halogenation of aliphatic carboxylic acids.
通常、ハロゲン化反応液は未反応カルボン酸、モノハロ
ゲン化物、ジハロゲン化物、トリハロゲン化物等の組成
物であり、その組成は製造の目的により異っている。引
続き、該反応液を高真空下にて精留し、製品化している
。Usually, the halogenation reaction solution is a composition of unreacted carboxylic acid, monohalide, dihalide, trihalide, etc., and its composition varies depending on the purpose of production. Subsequently, the reaction solution is rectified under high vacuum to produce a product.
ところで、該製品は例えば當温下、１〜４０日の短期間
で白濁物質を生成し、保存中に商品価値が劣化するため
長期保存が困Ｍであった。又、この白濁物質は再度精留
することにより除去できるが、再生品についても同様に
経時白濁を起すため従来、当業界ではこの対策に著しく
苦慮していた。一本発明者は、これらの事情を鑑みて、
脂肪族ハロゲンカルボン酸の長期保存を可能にするため
鋭意検討した結果、ハイドロキノン類を微量添加するこ
とにより、同課題を解決できることを見い出し、本発明
に到達した。By the way, this product generates a cloudy substance in a short period of 1 to 40 days at this temperature, and its commercial value deteriorates during storage, making it difficult to store it for a long period of time. Further, this cloudy substance can be removed by rectifying it again, but recycled products also become cloudy over time, so the industry has hitherto had great difficulty in taking measures against this problem. In view of these circumstances, the inventor of the present invention
As a result of intensive studies to enable long-term storage of aliphatic halogencarboxylic acids, it was discovered that the same problem could be solved by adding a trace amount of hydroquinones, and the present invention was achieved.
即ち、本発明は炭素数が３又は４を有する脂肪族ハロゲ
ンカルボン酸にハイドロキノン類を添加することを特徴
とする脂肪族ハロゲンカルボン酸の安定化方法である。That is, the present invention is a method for stabilizing an aliphatic halogen carboxylic acid, which is characterized by adding hydroquinones to an aliphatic halogen carboxylic acid having 3 or 4 carbon atoms.
（ここで、ハロゲンは塩素又は臭素を示す。）
本発明の方法を実施すれば、白濁物質、その生成及び防
止機構等はよく判らないが、脂肪族ハロゲンカルボン酸
において経時白濁による品質低下を完全に助＋１−．Ｌ
、長期の安定保存ができるので、その工業的両値ゆ大き
いと言える。(Here, halogen indicates chlorine or bromine.) If the method of the present invention is carried out, the quality deterioration due to cloudiness over time can be completely prevented in aliphatic halogen carboxylic acids, although the white cloudiness, its generation and prevention mechanism are not well understood. Nisuke+1-. L
Since it can be stored stably for a long period of time, it can be said that its industrial value is high.
本発明で対象となる炭素数が３又は４を有する脂肪族ハ
ロゲンカルボン酸は代表的にはα−クロルプロピオン酸
、β−クロルプロピオン酸、α、α−ジクロルプロピオ
ン酸、あるいはその混合物；α−ブロムプロピオン酸、
α、α−ジブロムプロピオン酸、あるいはその混合物；
α−クロル酪酸、γ−クロル酪酸、α−ブロム酪酸等が
例示される０本発明で使用されるハイドロキノン類は代
表的にはハイドロキノ／あるいはハイドロキノンモノメ
チルエーテル等が例示される。ノ１イドロキノン類の添
加９は脂肪族ハロゲンプロピオン酸に対し１０〜２，０
００ｐｐｌｎ、好ましくは５ｏ〜５００１Ｆが適してい
る。The aliphatic halogencarboxylic acids having 3 or 4 carbon atoms targeted in the present invention are typically α-chloropropionic acid, β-chloropropionic acid, α, α-dichloropropionic acid, or a mixture thereof; α -bromopropionic acid,
α, α-dibromopropionic acid, or a mixture thereof;
Examples include α-chlorobutyric acid, γ-chlorobutyric acid, α-bromobutyric acid, etc. Hydroquinones used in the present invention are typically exemplified by hydroquino/hydroquinone monomethyl ether. The addition of hydroquinones 9 is 10 to 2,0 to aliphatic halogen propionic acid.
00ppln, preferably 5o to 5001F are suitable.
ハイドロキノン類添加の態様は脂肪族ハロゲンカルボン
酸の種類によって異なるが、例えばα−クロルプロピオ
ン酸の如く液体の場合は常温にて添加後、攪拌溶解する
ことにより効果が得られる。The mode of addition of hydroquinones varies depending on the type of aliphatic halogencarboxylic acid, but for example, in the case of a liquid such as α-chloropropionic acid, the effect can be obtained by adding at room temperature and stirring and dissolving.
また、β−クロルプロピオン酸の如く常温で固体の場合
はハイドロキノン類を添加後、単に攪拌混合することに
よっても効果は得られるが、その混合物を融点以上に加
熱溶融し、ノーイドロキノン頬を均一に溶解することに
より、更に効果が向上する０
以下、実施例にて詳細を説明する。ここで安定性評価の
判断基準は次の通りであるＯ
○印； 液体状態で澄明（安定）
×印； 液体状態で白濁、不澄明（白濁物質、生成）
実施例１゜
精留直後のクロルプロピオン酸（原品：和光紬薬製試薬
）に７・イドロキノｙ類を添加、溶解後、室温にて安定
性テス）・を行った。結果を表−１に示す。In addition, in the case of β-chloropropionic acid, which is solid at room temperature, the effect can be obtained by simply stirring and mixing after adding hydroquinone. The effect is further improved by dissolving it in the following examples. Here, the criteria for stability evaluation are as follows: O mark: Clear in liquid state (stable) × mark: Cloudy, opaque and clear in liquid state (cloudy substance, formed) Example 1 Chlor immediately after rectification After adding and dissolving 7.hydroquino-y in propionic acid (original product: reagent manufactured by Wako Tsumugi Pharmaceutical Co., Ltd.), a stability test was conducted at room temperature. The results are shown in Table-1.
実施例２゜
精留直後のブロムプロピオン酸（原品：和光紬薬製試薬
）に溶融状態でノ・イドロキノン類を添加、溶解し、室
温にて安定性テストを行ったＯ結果を表−２に示す。Example 2゜No-hydroquinones were added and dissolved in the molten state to bromopropionic acid (original product: reagent made by Wako Tsumugi Pharmaceutical Co., Ltd.) immediately after rectification, and a stability test was conducted at room temperature. The O results are shown in Table 2. Shown below.
実施例３゜
精留直後のγ−クロル酪酸（原品：和光紬薬製試薬）に
ハイドロキノン類を添加、溶解後、室温にて安定性テス
トを行った。結果を表−３に示す。Example 3 Hydroquinones were added to and dissolved in γ-chlorobutyric acid (original product: Wako Tsumugi reagent) immediately after rectification, and a stability test was conducted at room temperature. The results are shown in Table-3.
Claims (1)
ハイドロキノン類を添加することを特徴とする脂肪族ハ
ロゲンカルボン酸の安定化方法。 （ここでハロゲンは、塩素又は臭素を示す。）[Scope of Claims] A method for stabilizing an aliphatic halogencarboxylic acid, which comprises adding hydroquinones to an aliphatic halogencarboxylic acid having 3 or 4 carbon atoms. (Here, halogen refers to chlorine or bromine.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17647083A JPS6067443A (en) | 1983-09-26 | 1983-09-26 | Method for stabilizing aliphatic halogenated carboxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17647083A JPS6067443A (en) | 1983-09-26 | 1983-09-26 | Method for stabilizing aliphatic halogenated carboxylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6067443A true JPS6067443A (en) | 1985-04-17 |
| JPH048416B2 JPH048416B2 (en) | 1992-02-17 |
Family
ID=16014236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17647083A Granted JPS6067443A (en) | 1983-09-26 | 1983-09-26 | Method for stabilizing aliphatic halogenated carboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6067443A (en) |
-
1983
- 1983-09-26 JP JP17647083A patent/JPS6067443A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH048416B2 (en) | 1992-02-17 |
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